AQUEOUS ACTIVE INGREDIENT CONCENTRATE HAVING AN HERBICIDAL EFFECT

Abstract

The invention discloses an aqueous active compound concentrate comprising, in dissolved form: (a) 10 to 100 g/l of at least one 4-benzoyl-substituted pyrazole compound of the formula I or one of its agriculturally useful salts; in which R1; R2; R3; R4; R5 and R6 are as defined in the specification. (b) 50 to 250 g/l of at least one benzoic acid compound of the formula II or one of its agriculturally useful salts; in which R7and R8 are as defined in the specification. (c) 100 to 500 g/l of at least one nonionic surfactant S, selected from polyether compounds having repeat units derived from ethylene oxide, alkylpolyglycosides and mixtures thereof, where the polyether compound has a polyether group of formula III in which EO ; AO; Rx; x ; y are as defined in the specification.

Full Text

Description
The present invention relates to aqueous active compound concentrates having
herbicidal action comprising, in dissolved form:
a) at least one 4-benzoyl-substituted pyrazole compound of the formula I

in which
R1, R3 independently of one another are hydrogen, halogen, methyl,
halomethyl, methoxy, halomethoxy, methylthio, methylsulfinyl or
methylsulfonyl;
R2 is a 5-membered heterocyclic radical which is unsubstituted or carries 1,
2, 3 or 4 substituents selected from the group consisting of halogen,
C1-C6-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and
C1-C4-alkylthio;
R4 is hydrogen, halogen or methyl;
R5 is C1-C6-alkyl, C3-C6-cycloalkyl or C3-C6-cycloalkylmethyl; and
R6 is hydrogen or C1-C4-alkyl;
or one of its agriculturally useful salts; and
b) at least one benzoic acid derivative of the formula II

in which
R7 is hydrogen, halogen, hydroxyl or methoxy and
R8 is hydrogen, halogen or amino;
or one of its agriculturally useful salts; and

Pure crops of agriculturally interesting useful plants are required for efficient and
profitable practice of industrialized agriculture and for ensuring a consistent product
quality. The selective sensitivity of different plant groups with respect to certain
metabolic inhibitors or other cell toxins may be utilized for the targeted control of
unwanted foreign vegetation (growth of harmful plants) on the areas under agricultural
cultivation. Here, it is desirable in principle to enhance both the absolute efficacy and
the specificity of the active compounds used (herbicides) against harmful plants.
The specificity and, within certain limits, the absolute efficacy can be enhanced by
using combinations of a plurality of specific active compounds which attack at different
points of the metabolism of the target plants. If the activity of the combination exceeds
the sum of the individual activities significantly, this is referred to as synergism
(occasionally also as superadditive effects).
The absolute efficacy of crop protection agents can be increased by various types of
accompanying substances and auxiliaries which may enhance the desired activity in
various ways. Further additives may be used to simplify handling, to increase storability
and to improve other product properties.
An important role in the formulation of herbicidally active compounds is played by
"adjuvants". These are to be understood as auxiliaries which increase the activity of an
active compound and/or its selectivity for the harmful plant, but which per se have
minute, if any, activity against the harmful plant to be controlled. In many cases, the
activity of adjuvants for herbicides is based on their surface activity which improves
contact of the application form of the active compound, in general an aqueous active
compounC1-Containing spray liquor, with the surface of the plant and, by reducing
surface tension, improves penetration of the application form and thus the active
compound into the soil. Whether a particular surfactant acts as adjuvant, i.e. whether it
achieves enhanced activity or selectivity, frequently depends on the nature of the active
compound.
In general, adjuvants are added only immediately prior to the application of the active
compound of the application form, for example the spray liquor. However, in principle,
they may also be a constituent of an active compound formulation, and this is preferred
for reasons of handling and application safety. However, many active compounds are
incompatible with the customary surfactants, in particular on prolonged storage. Here,
incompatibility means any chemical or physicochemical reduction of activity or
reduction of practical applicability, which may be the result either of direct chemical
reaction of active compounds and auxiliaries or of a reduced availability of the active

compounds in the mixture, for example by formation of precipitates which are poorly
soluble under application conditions or by demixing of the formulation. There may also
be incompatibility with the other constituents of the formulation. Accordingly, it is
regularly necessary to match adjuvants and the active compound to be formulated, and
also the other constituents of the formulation.
WO 99/63823 discloses to improve the activity of 4-benzoyl-substituted pyrazole
compounds by adding relatively large amounts of nitrogenous fertilizers and adjuvants.
Thus, on application, large amounts of fertilizer are applied, which may have a negative
effect on selectivity.
WO 00/53014 discloses to increase the activity of herbicidal 4-benzoyl-substituted
pyrazole compounds by using an adjuvant which comprises a mixture of a fatty acid, a
phosphoric acid or sulfuric acid semiester of a monohydroxy functional polyalkyl ether
and a C1-C5-alkyl C10-C20-alkanoate. When this adjuvant is incorporated into aqueous
concentrate formulations of the 4-benzoyl-substituted pyrazole compounds, there may
be homogeneity problems. Also, the active compound may precipitate in the spray
liquor obtained on dilution. For this reason, such adjuvants are added only shortly prior
to application of the aqueous spray liquor (tank mix method).
WO 99/65314 describes inter alia synergistically active herbicide mixtures comprising a
herbicidally active 4-benzoyl-substituted pyrazole compound, for example one of the
compounds I defined at the outset, and a synergist, for example a herbicide from the
group of the benzoic acid compounds, for example one of the compounds of the
formula II defined at the outset. However, the herbicidally active benzoic acid
compounds frequently also damage useful plants. The incorporation of adjuvants into
water-soluble concentrate formulations of active compound mixtures comprising
4-benzoyl-substituted pyrazole compounds of the formula I and benzoic acid
compounds of the formula II is frequently associated with problems. In particular if
relatively large amounts of adjuvants and/or higher concentrations of benzoic acid
compound are used, there are frequently inhomogeneities or solids separating out.
Accordingly, it was an object of the present invention to provide an aqueous
homogeneous formulation comprising at least one compound of the formula I together
with at least one compound of the formula II and a relatively large amount of an
adjuvant, which formulation is storage-stable. In addition, the formulation was to be
dilutable with water without any problems.

Surprisingly, it has now been found that these and other objects are achieved by using
the nonionic surfactants S described below.
Accordingly, the present invention provides aqueous active compound concentrates
comprising, in dissolved form:
a) at least one 4-benzoyl-substituted pyrazole compound of the formula I, as defined
at the outset;
b) at least one benzoic acid compound of the formula II, as defined at the outset;
and
c) at least one nonionic surfactant S, selected from polyether compounds having
repeat units derived from ethylene oxide, alkylpolyglycosides and mixtures
thereof.
The active compound concentrates according to the invention are homogeneous
aqueous solutions of the active compounds of the formulae I and II. The concentrates
are storage-stable and, even after prolonged storage, show no tendency for solids to
separate off, even when large amounts of surfactant S are present. The active
compound concentrates are easy to handle and can be diluted with water without
active compounds separating off. Moreover, it has been found that, by using these
nonionic surfactants S, it is possible not only to increase the herbicidal activity of the
active compound mixture to exceed the already known synergy of the active
compounds I and II, but also to reduce the damaging effect of the active compounds of
the formula II on the agriculturally useful plants.
Here and below, alkyl and the alkyl moieties in alkylcarbonyl, alkoxy, alkylthio and
alkylphenyl, are straight-chain or branched saturated hydrocarbon radicals.
Correspondingly, alkenyl denotes straight-chain or branched hydrocarbon radicals
which are monounsaturated. Haloalkyl and the haloalkyl moieties in haloalkoxy denote
straight-chain or branched alkyl radicals in which 1 or more, for example 1, 2, 3, 4, 5 or
else all, hydrogen atoms are replaced by halogen, in particular by chlorine or fluorine.
Phenylalkyl denotes a phenyl radical which is attached via an alkyl group to the
remainder of the molecule. Cycloalkyl denotes cyclic saturated hydrocarbon radicals.
The prefix Cn-Cm indicates in each case the number of possible carbon atoms.
Examples of alkyl are C1-C4-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl,
1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, furthermore C1-C6-alkyl which, in

generally covalently attached to an organic radical (basic moiety) or attached via an
ether oxygen atom to a macromolecule.
The covalent attachment of the macrogol moiety (moieties) to the basic moiety is
generally via an oxygen, sulfur or nitrogen atom, preferably via an oxygen atom. The
basic moiety is typically an organic radical having generally 4 to 40, frequently 6 to 30
and in particular 10 to 22 carbon atoms, where the basic moiety may optionally also
have one or more functional groups, for example 1 or 2 carbonyloxy groups (C(=0)-O-
groups) and/or 1, 2, 3 or 4 OH groups and/or 1, 2, 3, 4, 5 or 6 nitrogen atoms.
Examples of radicals suitable as basic moiety are C8-C30-alkyl, C8-C30-alkenyl,
C4-C30-a!kanediyl, C8-C30-alkantriyl, C5-C10-cycloalkyI, C5-C10-cycloalkanediyl,
α,α'-[bisphenyl-C1-C4-alkane]diyl, α,α'-[biscyclohexyl-C1-C4-alkane]diyl, mono- and
di-C4-C20-alkylphenyl, in particular butylphenyl, 4-tert-butylphenyl, hexylphenyl,
octylphenyl, nonylphenyl, dodecylphenyl, tridecylphenyl, C8-C20-alkylcarbonyl, benzoyl,
C1-C20-alkylbenzoyl, naphthyl which may optionally have 1, 2 or 3 C1-C10-alkyl groups,
mono-, di- and tristyrylphenyl, furthermore radicals derived from sorbitan esters, from
alkylpolyglycosides, from mono- or diglycerides and also from (oligo)alkyleneimines.
Alkyl(poly)glycosides or alkylpolyglucosides are to be understood as meaning
compounds having one or more, in particular one, alkyl radical, in particular a
C6-C22-alkyl radical, which is attached via an oxygen atom to a mono- or
oligosaccharide radical, for example to a mono-, di- or trisaccharide radical. Here, the
saccharide units are typically derived from glucose. Preferred alkyl(poly)glycosides are
those having on average 1 to 2 glucose units. In general, these are mixtures. In
polyether compounds having a basic moiety derived from alkyl(poly)glycosides, the at
least one macrogol moiety replaces at least one of the non-esterified hydroxyl groups
of the mono- or oligosaccharide radical.
Sorbitan esters are to be understood as meaning esters, in particular mono- or
diesters, of sorbitol with saturated or unsaturated aliphatic carboxylic acids, in particular
saturated or unsaturated fatty acids having 8 to 22 carbon atoms. In polyether
compounds having a basic moiety derived from sorbitol esters, the at least one
macrogol moiety replaces at least one of the non-esterified hydroxyl groups of the
sorbitan.
Mono- and diglycerides are to be understood as meaning mono- or diesters of glycerol
or mixtures thereof with saturated or unsaturated aliphatic carboxylic acids, in particular
saturated or unsaturated fatty acids having 8 to 22 carbon atoms. In polyether
compounds having a basic moiety derived from mono- or diglycerides, the at least one

macrogol moiety replaces at least one of the non-esterified hydroxy! groups of the
glycerol.
Radicals derived from (oligo)alkyleneimines are to be understood as meaning radicals
derived from alkylenediamines or oligomeric iminoalkyleneamines, such as mono-, di-,
tri- and tetraethyleneimine or mono-, bis-, tris- or tetrakis-(3-aminopropyl)ethylene-
diamine. In polyether compounds having a basic moiety derived from (oligo)alkylene-
imines, the at least one macrogol moiety replaces at least one NH hydrogen atom of
the (oligo)alkyleneimine.
The percentage of the EO repeat units of the total weight of the polyether compounds
is typically in the range of from 10 to 90% by weight and in particular in the range of
. from 30 to 85% by weight.
In general, the polyether compounds have an HLB according to Griffin of from 1.5 to
19.5, preferably from 1.5 to 14.0, particularly preferably from 2 to 10, very particularly
preferably from 3 to 7. Here, the numbers mentioned always refer to a mean value.
Here, "HLB according to Griffin" means the ratio of the hydrophilic and hydrophobic
moieties of the molecule, expressed as the proportion of the ethylene oxide moiety with
respect to the molecular weight of the entire molecule, multiplied by twenty.
Polyether compounds whose polyether groups also contain, in addition to the repeat
units derived from ethylene oxide, other repeat units, i.e. repeat units derived from
C3-C5-alkylene oxides and/or styrene oxide, generally have a modified HLB in the
range of from 5 to 19.5, preferably from 5 to 16.0, particularly preferably from 7 to 14,
very particularly preferably from 10 to 14; here, the numbers mentioned always refer to
a mean value. Here, "modified HLB" means the ratio of the hydrophilic and hydrophobic
moieties of the molecule, to take into account the different hydrophilicity of ethylene
oxide units and other repeat units in the polyether chain, expressed as the proportion of
the ethylene oxide moiety with respect to the molecular weight of the entire molecule,
multiplied by twenty, plus the proportion of the other repeat units with respect to the
molecular weight of the entire molecule, multiplied by ten.
The molecular weight of the polyether compounds may vary over wide ranges and is
typically in the range of from 200 to 10 000 Dalton and in particular in the range of from
300 to 5000 Dalton (in each case number average), unless indicated otherwise.
Preferably, the quotient of mass average and number average of the molecular weight
is in the range of from 0.9 to 1.6, preferably in the range of from 1.0 to 1.4 and
particularly preferably in the range of from 1.1 to 1.3.

The polyether groups in the polyether compounds S can generally be described by the
general formula III
Rx-(EO)x (AO)y]- (III)
in which
EO is -CH2-CH2-O-;
AO is -CHRa-CRbRc-O-, with any arrangement of EO units and AO units within the
chain being possible, including a random arrangement or a block arrangement;
Rx is hydrogen, C1-C10-alkyl, C5-C10-cycloalkyl, benzyl or C1-C20-alkylcarbonyl and is
attached via the oxygen atom of an EO group or an AO group;
x is an integer whose number average is in the range of from 1 to 150, in particular
from 2 to 8.0.and particularly preferably from 3 to 40;
y is an integer whose number average is in the range of from 0 to 150, in particular
from 0 to 50 and especially from 0 to 30, where the number average of the sum
of x and y is generally in the range of from 2 to 150, in particular in the range of
from 3 to 80 and particularly preferably in the range of from 5 to 40;
Ra, Rb independently of one another are hydrogen or methyl and in particular hydrogen;
and
Rc is hydrogen, C1-C4-alkyl, especially methyl or phenyl,
where at least one of the radicals Ra, Rb and Rc is different from hydrogen.
In formula III, AO and EO are repeat units (monomer units) from which the polyether
group is constructed. If the polyether groups of formula III comprise repeat units AO,
the repeat units EO and AO may be in any arrangement, for example in a block
arrangement where relatively long sequences of EO units are linked to relatively long
sequences of AO units, or in a random arrangement, or in mixed forms of random
arrangement and block arrangement. If the polyether groups III have a block
arrangement of AO blocks and EO blocks, it is preferred for the polyether group to
consist of 2 or 3 and in particular 2 blocks. Here, the indices x and y indicate the
number of the respective repeat units within the polyether group. Since the polyether
compounds are generally not molecularly uniform compounds but mixtures of
compounds having various polyether chains which typically differ in the number of the
respective repeat units, x and y are typically mean values (number average), in each
case based on the total amount of repeat units EO and AO, respectively, in the
polyether compound.
Groups AO which may be mentioned are, for example, radicals derived from propylene
oxide (PO; Ra = Rb = hydrogen and Rc = methyl), butylene oxide (BO; Ra = Rb =

hydrogen and Rc = ethyl), isobutylene oxide (IBO; Ra = hydrogen and Rb = Rc =
methyl), pentylene oxide (PPO; Ra = Rb = hydrogen and Rc = propyl), hexylene oxide
(HO; Ra = Rb = hydrogen and Rc = butyl) and styrene oxide (StO; Ra = Rb = hydrogen
and Rc = phenyl). If the polyether group has radicals AO, these are preferably derived
from propylene oxide.
From among the polyether compounds, preference is given to those having one or
more groups of the formula III in which Rx is hydrogen or C1-C10-alkyl, in particular
hydrogen or C1-C4-alkyl, especially methyl. In a preferred embodiment of the invention,
the polyether groups are terminally modified, i.e. Rx is a radical different from hydrogen.
In this case, Rx is preferably C1-C10-alkyl, in particular C1-C4-alkyl and especially
methyl. Suitable as substance S are in particular also polyether compounds in which Rx
is C1-C20-alkylcarbonyl. According to a particularly preferred embodiment, the polyether
compounds are not terminally modified, i.e. Rx is hydrogen.
In a preferred embodiment, the polyether compound is selected from ethylene
oxide/propylene oxide copolymers (hereinbelow referred to as EO/PO copolymers).
These are to be understood as meaning polyether compounds predominantly, i.e. to at
least 90% by weight, constructed of repeat units EO and PO (= CH2-CH(CH3)-0).
Formally, these are compounds in which two polyether groups of the formula III in
which y * 0 and AO is CH2-CH(CH3)0 are attached to one another via an ether oxygen
atom or via a C4-C10-alkanediyl group. From among these, preference is given to
ethylene oxide/propylene oxide block copolymers in which the number of the PO blocks
and the EO blocks is preferably 2 or in particular 3. Especially preferred are triblock
copolymers of the formulae below

Here, the unit [POy1]A[POy2] is seen as a PO block. In the formulae, Rx, EO, PO, x and
y have the meanings mentioned above, and Rx has one of the meanings given for Rx.
Independently of one another, the indices x1 and x2 have one of the values given for x.
The indices y1 and y2 are different from 0 and, besides, independently of one another
have one of the values given for y. The index y3 typically denotes a value of from 2 to
160, in particular a value of from 4 to 100 and especially from 10 to 80. The index x3
typically denotes a value of from 4 to 200, in particular a value of from 10 to 100 and

especially of from 10 to 80. A is C4-C10-alkanediyl or C5-C10-cycloalkanediyl. Y is
oxygen or a radical NR in which R is hydrogen, C1-C4-alkyl or a group of the formula III.
Rx and Rx are in particular hydrogen or C1-C10-alkyl. The number average molecular
weight of the EO/PO copolymers is preferably in the range of from 300 to 10 000, in
particular in the range of from 500 to 5000, Dalton. The percentage of EO repeat units
is typically in the range of from 10 to 90% by weight, in particular in the range of from
20 to 80% by weight, and the percentage of the PO repeat units is in the range of from
10 to 90% by weight, in particular in the range of from 20 to 80% by weight, in each
case based on the total weight of the EO/PO copolymer.
According to a further preferred embodiment of the invention, the polyether compound
is selected from polyether compounds having at least one, for example 1, 2, 3 or 4, in
particular 1 or 2, and especially one, polyether group of the formula III which is (are)
attached covalently via an oxygen, sulfur or nitrogen atom to a hydrocarbon radical
having 8 to 40 carbon atoms, in particular 10 to 30 carbon atoms and which optionally
also has 1 or 2 carbonyloxy groups and/or 1, 2, 3 or 4 OH groups.
Preferred polyether compounds of this embodiment are:
polyethoxylates and poly(ethoxylate-co-propoxylate)s of C8-C22-alkanols, in
particular C10-C18-alkanols. These are to be understood as meaning
compounds having a group of the formula III which is attached via an oxygen
atom to a C8-C22-alkyl radical, the group of the formula III having either
exclusively EO repeat units or EO and PO repeat units;
polyethoxylates and poly(ethoxylate-co-propoxylate)s of fatty acids. These
are to be understood as meaning compounds having a group of the formula
III which is attached via an oxygen atom to a fatty acid radical, generally a
C8-C22-alkylcarbonyl radical or a C8-C22-alkenylcarbonyl radical, the group of
the formula III having either exclusively EO repeat units or EO and PO repeat
units;
polyethoxylates and poly(ethoxylate-co-propoxylate)s of fatty amines. These
are to be understood as meaning compounds having one or two groups of the
formula III which are attached via a nitrogen atom to a hydrocarbon radical
derived from a fatty amine, generally a C8-C22-alkyl radical, the group of the
formula III having either exclusively EO repeat units or EO and PO repeat
units;
polyethoxylates and poly(ethoxylate-co-propoxylate)s of mono- and
diglycerides of aliphatic C8-C22-monocarboxylic acids. These are to be
understood as meaning compounds having one or two groups of the formula
III which are attached via an oxygen atom to a radical derived from a mono-

or diglyceride of a saturated or unsaturated aliphatic C8-C22-monocarboxyiic
acid, the group of the formula III having either exclusively EO repeat units or
EO and PO repeat units;
polyethoxylates and poly(ethoxylate-co-propoxylate)s of sorbitan esters of
saturated or unsaturated aliphatic C8-C22-monocarboxylic acids. These are to
be understood as meaning compounds having one or two groups of the
formula III which are attached via an oxygen atom to a radical derived from a
sorbitan mono- or diester of an aliphatic C8-C22-monocarboxylic acid, the
group of the formula III having either exclusively EO repeat units or EO and
PO repeat units;
polyethoxylates and poly(ethoxylate-co-propoxylate)s of alkylphenols. These
are to be understood as meaning compounds having a group of the formula
III which is attached via an oxygen atom to an alkylphenyl radical, in particular
a mono- or di-C4-C20-alkylphenyl radical, the group of the formula III having
either exclusively EO repeat units or EO and PO repeat units;
polyethoxylates and poly(ethoxylate-co-propoxylate)s of mono-, di- and tri-
styrylphenols. These are to be understood as meaning compounds having a
group of the formula III which is attached via an oxygen atom to a mono-, di-
or tristyrylphenyl radical, the group of the formula III having either exclusively
EO repeat units or EO and PO repeat units;
polyethoxylates and poly(ethoxylate-co-propoxylate)s of alkyl(poly)glycosides
and mixtures thereof. These are to be understood as meaning compounds
having one or more, for example 1, 2, 3 or 4, groups of the formula III which
are attached via an oxygen atom to a radical derived from an
alkyl(poly)glycoside, the group of the formula III having either exclusively EO
repeat units or EO and PO repeat units.
Polyethoxylates and poly(ethoxylate-co-propoxylate)s of oligo- and polyalkyleneimines,
in particular those of the compounds of the formula NH2-(A-NH)k-A'-NH2 in which A and
A' independently of one another are ethane-1,2-diyl or propane-1,3-diyl and k is in the
range of from 1 to 100 are also suitable, in addition to the polyether compounds
mentioned above.
The polyethoxylates and poly(ethoxylate-co-propoxylate)s mentioned above may be
terminally capped, i.e. the radical Rx is different from hydrogen and is in particular
C1-C10-alkyl, preferably C1-C4-alkyl and especially methyl. Preference is also given to
those of the abovementioned polyethoxylates and poly(ethoxylate-co-propoxylate)s in
which the radical Rx is hydrogen.

The number average molecular weight of the abovementioned polyethoxylates and
poly(ethoxylate-co-propoxylate)s is preferably in the range from 200 to 5000, in
particular in the range of from 300 to 3000, Dalton. The percentage of EO repeat units
is typically in the range of from 7 to 98% by weight, in particular in the range of from 10
to 80% by weight and especially from 15 to 70% by weight, based on the total weight of
the polyethoxylates and poly(ethoxylate-co-propoxylate)s. The PO and EO repeat units
in the poly(ethoxylate-co-propoxylate)s may be arranged at random or in blockwise
fashion, the latter being preferred. In particular, the poly(ethoxylate-co-propoxylate)s
have a block of EO repeat units attached to the basic moiety of the compound and a
block of PO repeat units which carries the radical Rx. From among these, particular
preference is given to those polyethoxylates having a mean degree of ethoxylation
(corresponding to the number average of x) in the range of from 3 to 50, in particular
from 4 to 30 and especially from 5 to 20. From among the poly(ethoxylate-co-
propoxylate)s, preference is given to those having a mean degree of ethoxylation in the
range of from 2 to 49, preferably in the range of from 3 to 29 and especially in the
range of from 4 to 19, and a mean degree of propoxylation (corresponding to the
number average of y) in the range of from 1 to 48, in particular in the range of from 1 to
27 and especially in the range of from 1 to 16, the total degree of alkoxylation
(corresponds to the number average of the sum x + y) preferably being in the range of
from 3 to 50, especially from 4 to 30 and very particularly preferably in the range of
from 5 to 20.
According to a particularly preferred embodiment, the polyether compound is a
polyalkoxylated C8-C30-alkanol. Such compounds can be described by the general
formula IV

in which EO, AO, x, y, and Rx have the meanings mentioned above and R11 is a
straight-chain or branched alkyl radical having 8 to 30 carbon atoms, in particular 8 to
22 carbon atoms and especially 10 to 18 carbon atoms. Preferred straight-chain alkyl
radicals R11 are derived from alkanols having 8 to 22 carbon atoms, in particular 10 to
18 carbon atoms. Particularly preferred alkyl radicals R" are branched at least once
and have 8 to 22 carbon atoms, in particular 10 to 18 carbon atoms. Examples of R11
are straight-chain radicals, such as n-octyl, n-decyl, n-dodecyl, n-tridecyl, n-tetradecyl,
n-pentadecyl, n-hexadecyl, n-octadecyl, and branched radicals, such as isononyl,
isoundecyl, isotridecyl, isopentadecyl, 2-ethylhexyl and 2-propylheptyl. Here, it has to
be kept in mind that in the compounds IV the radicals R11 may also be mixtures of
different radicals having preferably the same or a similar number of carbons and

different degrees of branching, as obtained in the industrial preparation of the alkanols
on which the compounds IV are based.
From among the polyether compounds of the formula IV, preference is given to those
in which AO, if present, is CH2CH(CH3). From among these, particular preference is
given to those compounds in which x is a number whose number average is in the
range of from 2 to 49, preferably in the range of from 3 to 39 and especially in the
range of from 4 to 29, y is a number whose number average is in the range of from 1
to 48, in particular in the range of from 1 to 37 and especially in the range of from 1 to
26, and the number average of the sum x + y is in the range of from 3 to 50, especially
in the range of from 4 to 40. In particularly preferred poly(ethoxylate-co-propoxylate)s
of the formula IV, the EO units and the PO unit are arranged in the form of two blocks.
The polyether compound IV may be terminally capped, i.e. Rx is different from
hydrogen and is preferably C1-C10-alkyl, in particular C1-C4-alkyl and especially methyl.
R" is in particular hydrogen.
According to a further particularly preferred embodiment, the polyether compound is a
polyalkoxylated alkylphenol or a polyalkoxylated mono-, di- ortristyrylphenol. Such
compounds can be described by the general formula V

in which EO, AO, x, y, and Rx have the meanings mentioned above and R12 is a phenyl
radical which carries one or two straight-chain or branched alkyl radicals having
generally 4 to 20 carbon atoms, in particular 6 to 16 carbon atoms, or 1, 2 or 3 radicals
derived from styrene. Examples for alkyl radicals on phenyl include n-butyl, tert-butyl,
n-hexyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, isononyl,
undecyl, tridecyl, 2-ethylhexyl and 2-propylheptyl.
From among the polyether compounds of the formula V, preference is given to those in
which Rx in formula III is C1-C10-alkyl and AO, if present, is CH2CH(CH3). From among
these, particular preference is given to those compounds in which x is a number whose
number average is in the range of from 2 to 49, preferably in the range of from 3 to 29
and especially in the range of from 4 to 19, y is a number whose number average is in
the range of from 1 to 48, in particular in the range of from 1 to 27 and especially in the
range of from 1 to 16, and the number average of the sum x + y is in the range of from
3 to 50, especially from 4 to 30 and very particularly preferably in the range of from 5 to
20. In particularly preferred poly(ethoxylate-co-propoxylate)s of the formula V, the EO
units and the PO unit are arranged in the form of two blocks.

In a second preferred embodiment, the substance S comprises at least one
alkylpolyglycoside. In this embodiment, the percentage of the alkylpolyglycoside in
substance S is typically at least 90% by weight. In a further preferred embodiment, the
substance S is a mixture of alkylpolyglycoside and at least one polyether compound, in
particular a polyether compound of the formula IV or V. In this case, the weight ratio of
alkylglycoside to polyether compound is typically in the range of from 9:1 to 1:9, in
particular in the range of from 2:8 to 8:2.
The abovementioned compounds S are known to the person skilled in the art and
commercially available. Typical commercial products of the formula IV are available, for
example, from BASF under the common trade name of the "Lutensols", where,
depending on the basic moiety, a distinction is made between Lutensols of series A,
AO, AT, ON, AP, XP, XL, TO and FA. Further added numbers indicate the degree of
ethoxylation. Thus, for example, "Lutensol AO 8" is a C13-15-oxoalcohol having eight EO
units. "Lutensol FA" is a group of alkoxylated amines.
Further examples of polyether compounds suitable according to the invention are
products from Akzo, for example the "Ethylan" series based on straight-chain or
branched alcohols. Thus, for example "Ethylan SN 120" is a C10-12-alkohol having ten
EO Units, and "Ethylan 4 S" is a C12-14-alcohol having four EO units.
Further examples of polyalkoxylates suitable according to the invention are furthermore
the "IMP" products from Akzo (previously Witco), which are based on nonylphenols.
Polyether compounds suitable according to the invention are also "narrow range"
products. Here, the term "narrow range" refers to a narrow distribution of the number of
EO units. These include, for example, products of the "Berol" series from Akzo.
Furthermore according to the invention are sorbitan ester ethoxylates, for example
"Armotan AL 69-66 POE(30) sorbitan monotallate", i.e. unsaturated fatty acids
esterified with sorbitol and then ethoxylated.
In a preferred embodiment of the invention, the aqueous active compound concentrate
comprises components a) and b) in the form of their dissolved salts, in particular in the
form of their dissolved alkali metal or ammonium salts, preferably in the form of their
dissolved sodium, potassium or ammonium salts. The pH of the aqueous active
compound concentrate is preferably at least pH 8.0 and is in particular in the range of
pH 8.0 to 10.0, particularly preferably in the range of pH 8.0 to 9.0.

The present invention relates in particular to aqueous active compound concentrates of
compounds of the formula I in which R1 and R3 independently of one another are
preferably halogen, methyl, methylthio, methylsulfinyl or methylsulfonyl. R2 is in
particular a radical selected from the group consisting of thiazol-2-yl, thiazol-4-yl,
thiazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 4,5-dihydroxyisoxazol-3-yl,
4,5-dihydroisoxazol-4-yl and 4,5-dihydroisoxazol-5-yl, where the radicals mentioned
above are unsubstituted or may be substituted in the manner mentioned above and are
in particular unsubstituted or may carry 1 or 2 methyl groups as substituents. R2 is in
particular selected from the group consisting of isoxazol-5-yl, 3-methyiisoxazol-5-yl,
4,5-dihydroisoxazol-3-yl, 5-methyl-4,5-dihydroisoxazol-3-yl, 5-ethyl-4,5-dihydro-
isoxazol-3-yl and 4,5-dimethyl-4,5-dihydroisoxazol-3-yl selected radical. R4 is in
particular hydrogen. R5 is in particular methyl. R6 is in particular hydrogen or methyl. R1
is in particular chlorine, methyl or methylsulfonyl, R2 is hydrogen or 4,5-
dihydroisoxazol-3-yl, R3 is chlorine or methylsulfonyl, R4 is hydrogen, R5 is methyl and
R6 is hydrogen or methyl.
In a particularly preferred embodiment of the invention, R1 is methyl, R2 is 4,5-dihydro-
isoxazol-3-yl, R3 is methylsulfonyl, R4 is hydrogen, R5 is methyl and R6 is hydrogen, i.e.
the component a) comprises 4-[2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-
benzoyl]-1-methyl-5-hydroxy-1H-pyrazole (common name: topramezone).
The present invention relates in particular to aqueous active compound concentrates of
compounds of the formula II in which R7 is hydrogen or methoxy and R8 is hydrogen,
chlorine or amino. R7 is in particular methoxy. In a particularly preferred compound of
the formula II, R7 is methoxy and R8 is hydrogen. In another particularly preferred
compound of the formula II, R7 is hydrogen and R8 is amino. It is most preferred for
component b) to comprise 3,6-dichloro-ortho-anisic acid (common name: dicamba).
With utmost preference, the aqueous liquid formulation comprises, as component a),
4-[2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-benzoyl]-1-methyl-5-hydroxy-
1H-pyrazole in dissolved form and, as component b), 3,6-dichloro-ortho-anisic acid in
dissolved form.
The concentration of 4-benzoyl-substituted pyrazole compounds of the formula I in the
active compound concentrate according to the invention is generally from 10 to 100 g/l
and in particular from 25 to 80 g/l. The concentration of benzoic acid compound of the
formula II in the active compound concentrate according to the invention is generally
from 50 to 250 g/l and in particular from 80 to 200 g/l and especially from 140 to
160 g/l. The total concentration of nonionic surfactant S in the aqueous active

compound concentrates according to the invention is generally in the range of from 100
to 300 g/l, in particular in the range of from 200 to 400 g/l.
In a particular embodiment of the invention, the aqueous liquid formulation comprises a
herbicidally active 4-benzoyl-substituted pyrazole compound of the formula I and a
herbicidally active benzoic acid derivative of the formula II in a relative mass ratio of
from 1:25 to 2:1, preferably from 1:10 to 1:1 and particularly preferably from 1:5 to 1:3.
In a particular embodiment of the invention, the aqueous liquid formulation comprises
an active compound mixture of a herbicidally active 4-benzoyl-substituted pyrazole
compound of the formula I and a herbicidally active benzoic acid derivative of the
formula II and also a nonionic surfactant S in a mass ratio of total amount of the active
compound mixture to amount of substance S of from 1:10 to 3:1, preferably from
1:3 to 3:2 and particularly preferably from 2:3 to 1:1.
At least some of the compounds comprised by substance S are described in the prior
art.
The aqueous active compound concentrates according to the invention may
additionally aiso comprise further substances which are not directly relevant to the aim
of the composition, but which improve their applicability and/or practical properties.
Examples of these are in particular
- viscosity-regulating substances (thickeners),
- preservatives,
- antifoams,
- agents for adjusting the pH,
- antifreeze agents.
Such substances are familiar to the person skilled in the art. The total amount of such
substances will generally not exceed 10% by weight, based on the active compound
concentrate, and is typically in the range of from 0.1 to 10% by weight, based on the
total weight of the active compound concentrate.
The viscosity-modifying additives (thickeners) include in particular compounds which
are known to impart pseudoplastic flow behavior to aqueous formulations, i.e. high
viscosity in the state of rest and low viscosity in the state of motion. Suitable are, in
principle, all compounds used for this purpose in aqueous active compound
concentrates. Mention may be made, for example, of inorganic substances, such as
bentonite or attapulgite (for example Attaclay® from Engelhardt), and organic
substances, such as polysaccharides and heteropolysaccharides, such as Xanthan

Gum® (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T.
Vanderbilt), with Xanthan-Gum® being preferred. The amount of viscosity-modifying
additives is frequently from 0.1 to 5% by weight, based on the total weight of the active
compound concentrate.
Suitable antifoams are, for example, silicone emulsions (Silikon® SRE, from Wacker, or
Rhodorsil®, from Rhodia), long-chain alcohols, fatty acids, defoamers of the type of
aqueous wax dispersions, solid defoamers ("compounds"), organofluorine compounds
and mixtures thereof known to be suitable for this purpose. The amount of antifoam is
typically from 0.1 to 1 % by weight, based on the total weight of the active compound
concentrate.
Examples of preservatives are those based on isothiazolones, for example Proxel®
from ICI or Acticide® RS from Thor Chemie or Kathon® MK from Rohm & Haas. The
amount of preservatives, if present, is typically from 0.05 to 0.5% by weight, based on
the total weight of the active compound concentrate.
Suitable antifreeze agents are liquid alkanols, such as methanol, ethanol, isopropanol,
n-butanol, polyols, for example ethylene glycol, propylene glycol or glycerol. The
amount of antifreeze agents, if present, is generally from 1 to 10% by weight, based on
the total weight of the active compound concentrate.
If appropriate, the active compound concentrates according to the invention may
comprise agents for regulating the pH. Examples of such agents are bases, for
example alkali metal hydroxides, such as potassium hydroxide, sodium hydroxide,
sodium carbonate, potassium carbonate or ammonia, or else buffers, for example
alkali metal salts of weak inorganic or organic acids, such as, for example phosphoric
acid, boric acid, acetic acid, propionic acid, citric acid, furmaric acid, tartaric acid, oxalic
acid and succinic acid. The amount of agents for adjusting the pH, if present, is
generally from 0.01 to 3% by weight, based on the total weight of the active compound
concentrate.
The aqueous active compound concentrates according to the invention can be
prepared in a simple manner by dissolving the active compounds of the formulae I and
II in water or in an aqueous medium and adding substance S and, if appropriate, the
further ingredients of the active compound concentrate, if appropriate in dissolved form,
to the resulting solution. Here and below, an aqueous medium is to be understood as
meaning water which part of the other components optionally present of the active
compound concentrate, for example bases, buffers, preservatives, etc. Dissolution of

the active compounds of the formulae I and II may be carried out jointly or successively
in one apparatus or in several apparatuses, where in the latter case the resulting
aqueous solutions are combined. Frequently, for dissolving the active compounds, the
active compound I is suspended in water and the pH is adjusted to pH > 7, in particular
pH > 8, for example to pH 8 to pH 10, in particular to pH 8 to pH 9, by addition of a
base or a buffer, whereupon the active compound of the formula I goes into solution.
The solution obtained in this manner is then mixed with an aqueous solution of the
benzoic acid compound II or with an aqueous solution of a salt of the benzoic acid
compound II, for example an alkali metal salt or an ammonium salt. Alternatively, it is
also possible to suspend a mixture of active compound I and benzoic acid compound II
or one of the abovementioned salts of the benzoic acid compound II in water and then
adjusting the pH of the suspension by addition of a base or a buffer to the range
mentioned above, whereupon the active compounds of formulae I and II go into
solution. The other components of the active compound concentrate are then added to
the solutions obtained in this manner, which are homogenized in a customary manner,
for example by stirring, ultrasound.
The aqueous active compound concentrates obtained in this manner are particularly
suitable for controlling a large number of unwanted plants. The active compound
concentrates according to the invention are highly suitable for controlling unwanted
vegetation on non-crop areas, in particular at high application rates. In cereal crops
such as wheat, rye, barley, millet, oats or triticale, and also in corn, they act against
broad-leaved weeds and weed grasses without causing any significant damage to the
crop plants. This effect is observed especially at low application rates. The active
compound concentrates according to the invention are particularly suitable for
eliminating harmful plants in corn. Depending on the application method in question,
the active compound concentrates according to the invention can also be employed in
other crop plants for eliminating unwanted plants.
In addition, the active compound concentrates can also be used in crops which tolerate
the action of herbicides owing to breeding, including genetic engineering methods.
The active compound concentrates are generally applied in the form of an aqueous
spray liquor. To this end, the active compound concentrates according to the invention
are, depending on the application rate, diluted with water to a multiple of their volume,
for example 10- to 10 000-fold, in particular 20- to 1000-fold. The active compound
concentration (total amount of active compound) in the spray liquor is then typically in
the range of from 5 mg/l to 5 g/l, in particular from 0.01 to 1 g/l.

Application may be by the pre-emergence method, by the post-emergence method or
together with the seed of a crop plant. It is also possible to apply the active compounds
of the formulae I and II present in the active compound concentrates using the active
compound concentrates according to the invention by treating seed of a crop plant with
the active compounds of the formulae I and II and sowing the seed treated in this
manner. If the active compounds are less well tolerated by certain crop plants,
application techniques may be used in which the application forms prepared using the
active compound concentrates are sprayed, with the aid of the spraying equipment, in
such a way that as far as possible they do not come into contact with the leaves of the
sensitive crop plants, while the active compounds reach the leaves of unwanted plants
growing underneath, or the bare soil surface (post-directed, lay-by).
Based on the total amount of active compound I and II, .the application rates are,
depending on the control target, the season, the target plants and the growth stage,
from 0.001 to 3.0, preferably 0.005 to 0.5 kg/ha.
To widen the activity spectrum and to achieve synergistic effects, the active compound
concentrates may, prior to application, be mixed with numerous representatives of
other herbicidal or growth-regulating groups of active compounds and then applied
jointly, for example by the tank-mix method. Suitable components for mixtures are, for
example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and
derivatives thereof, aminotriazoles, anilides, (het)aryloxyalkanoic acid and derivatives
thereof, benzoic acid and derivatives thereof, benzothiadiazinones, 2-aroyl-1,3-
cyclohexanediones, 2-hetaroyl-1,3-cyclohexanediones, hetaryl aryl ketones,
benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic
acid and derivatives thereof, chloroacetanilides, cyclohexenone oxime ether
derivatives, diazines, dichloropropionic acid and derivatives thereof,
dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl
ethers, dipyridyls, halocarboxylic acids and derivatives thereof, ureas, 3-phenyluracils,
imidazoles, imidazoiinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles,
oxiranes, phenols, aryloxy- or heteroaryloxyphenoxypropionic esters, phenylacetic acid
and derivatives thereof, phenylpropionic acid and derivatives thereof, pyrazoles,
phenylpyrazoles, pyridazines, pyridinecarboxylic acid and derivatives thereof, pyrimidyl
ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,
triazolecarboxamides, uracils.
It may furthermore be beneficial to mix the active compound concentrates prior to
application with other crop protection agents, followed by joint application, for example
with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is

the miscibility with mineral salt solutions, which are employed for treating nutritional
and trace element deficiencies. It is also possible to add nonphytotoxic oils and oil
concentrates.
A Preparation examples
Examples 1 to 11: Preparation of an active compound concentrate according to the
invention (general procedure)
50 g of topramezone (active compound of the general formula I in which R1 and R5 are
methyl, R2 is 4,5-dihydrooxazol-3-yl, R3 is methylsulfonyl, R4 and R6 are hydrogen) and
160 g of dicamba (active compound of the formula II in which R7 is methoxy and R8 is
hydrogen) were suspended in 300 ml of water. By addition of 40% by weight strength
aqueous potassium hydroxide solution, the pH of the suspension was adjusted to
pH 8.5, 300 g of the substance S in question, if appropriate, in the form of an aqueous
mixture, and water ad 1 I were added to the resulting solution and the mixture was
homogenized with stirring for 2 h. This gave a clear solution comprising 50 g of
topramezone/l, 160 g of dicamba/l and 300 g of the substance S in question.
The following substances S were used:
S1: EO/PO triblock copolymer having OH end groups, a molecular weight of
3100 Dalton (number average) and an EO percentage of 42% by weight
S2: 2-ethylhexylpolyglucoside having 1.6-glucose units
S3: polyethoxylate of the formula CH3-O-(C2l-U-O)11-NH2
S4: ethoxylated polyimine having a degree of ethoxylation of 7 EO groups per nitrogen
atom, a molecular weight of about 14 000 (number average) and a percentage by
weight of EO groups of about 82% by weight
S5: ethoxylate-co-propoxylate of the formula R-O-(EO)x(PO)yH in which EO and PO
have the meanings mentioned above, R is straight-chain C13-C15-alkyl, y is 23 and
x is 10
S6: ethoxylate of the formula R-O-(EO)xH in which EO has the meanings mentioned
above, R is branched C10-alkyl and x is 7 (Lutensol ON 70)
S7: ethoxylate-co-propoxylate of the formula R-O-[(PO)y(EO)x]H in which EO and PO
are arranged randomly and have the meanings mentioned above, R is straight-chain
C9-C11-alkyl, y is 2 and x is 7.5
S8: ethoxylate-co-propoxylate of the formula R-O-(EO)x(PO)yH in which EO and PO
have the meanings mentioned above, R is branched C13-alkyl, y is 3 and x is 6
S9: ethoxylate of the formula R-O-(EO)xH in which EO has the meanings mentioned
above, R is branched C13-alkyl and x is 5 (Lutensol TO 5)

S10: ethoxylate of the formula R-O-(EO)xH in which EO has the meanings mentioned
above, R is branched C10-alkyl and x is 3 (Lutensol ON 30)
S11: ethoxylate of the formula R-O-(EO)xH in which EO has the meanings mentioned
above, R is branched C10-alkyl and x is 5 (Lutensol ON 50).
B Examination of the application properties
After 2 weeks of storage at 54°C, the active compound concentrates according to the
invention showed no visible changes.
The foaming tendencies were determined according to Ross-Miles (ASTM-D 1173 53).
It was low, in particular with the preparation formulated using S5.
C Examination of the herbicidal action
1. Herbicidal action against harmful grasses
The herbicidal action of the active compound concentrates according to the invention
against gramineous harmful plants was demonstrated by the following greenhouse
tests:
The culture containers used were plastic pots containing loamy sand with
approximately 3.0% of humus as the substrate. The seeds of the test plants were sown
separately for each species.
For the pre-emergence treatment, the active compound concentrates, which with water
to the desired application concentration, were applied directly after sowing by means of
finely distributing nozzles applied at the stated application rate. The containers were
irrigated gently to promote germination and growth and subsequently covered with
transparent plastic hoods until the plants had rooted. This cover causes uniform
germination of the test plants, unless this has been impaired by the active compounds.
For the post-emergence treatment, the test plants were first grown to a height of 3 to
15 cm, depending on the plant habit, and then treated with the active compound
concentrates with water to the desired application concentration (about 66 to 525 mg of
active compound/I). For this purpose, the test plants were either sown directly and
grown in the same containers, or they were first grown separately as seedlings and
transplanted into the test containers a few days prior to treatment.

Depending on the species, the plants were kept at temperatures of 10 - 25°C or
20 - 35°C. The test period extended over 2 to 4 weeks. During this time, the plants
were tended, and their response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of
the plants, or complete destruction of at least the above-ground parts, and 0 means no
damage, or normal course of growth.
The harmful plants (weeds) examined were grasses of the following species:
Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Panicum sp. (PANDI),
Panicum milliaceum (PANMI), Setaria faberr (SETFA), Setaria italica (SETIT), Setaria
lutescens (SETLU), Setaria viridis (SETVI).
Table 1 shows the results obtained for the post-emergence treatment (damage 20 or
21 days after treatment).

At the same application rate, the herbicidal activity of concentrates formulated according to
the invention against gramineous harmful plants exceeds the activity of a concentrate
without added surfactants considerably. In particular in the case of Setaria species,
complete control was possible.
2. Herbicidal action against non-gramineous harmful plants
Analogously to 1., the activity of formulations according to the invention against the non-
gramineous harmful plants Avena fatua, Sorghum bicolor was examined.
Table 2 shows the results obtained for the post-emergence treatment (examined 20 or 21
days after treatment).

3'. Herbicidal action against useful plants
Analogously to 1., the activity of active compound concentrates according to the invention
against the useful plants Zea mays (ZEAMX) of the cultivars "Dea" and "Helix" was
examined.
The plants were treated by the post-emergence method. The damage to the plants was
determined on day 6 or 8 (measurement A) and on day 20 or 21 (measurement B) after the
treatment. Otherwise, the procedure of Example 1 was adopted.

We Claim:
1. An aqueous active compound concentrate comprising, in dissolved form:
a) from 10 to 100 g/l of at least one 4-benzoyl-substituted pyrazole compound of
the formula I
in which
R1 is methyl;
R2 is 4,5-dihydroisoxazol-3-yl;
R3 is methylsulfonyl;
R4 is hydrogen;
R5 is methyl; and
R6 is hydrogen;
or one of its agriculturally useful salts;
b) from 50 to 250 g/l of at least one benzoic acid compound of the formula II
in which
R7 is methoxy and
R8 is hydrogen;
or one of its agriculturally useful salts; and
c) from 100 to 500 g/l of at least one nonionic surfactant S, selected from
polyether compounds having repeat units derived from ethylene oxide,
alkylpolyglycosides and mixtures thereof
in which the weight ratio of the total amount of active compound of pyrazole
compound of the formula I and benzoic acid compound of the formula II to surfactant
S is in the range of from 1:10 to 3:1,
where the composition comprises the 4-benzoyl-substituted pyrazole compound of the
formula I and the benzoic acid compound of the formula II in a weight ratio of from
1:25 to 2:1;
where the polyether compound has at least one polyether group of the formula III

in which
EO is -CH2-CH2-O-;
AO is -CHRa-CRbRc-O-;
Rx is hydrogen, C1-C10-alkyl, C5-C10-cycloalkyl, benzoyl or C1-C20-alkylcarbonyl and
is attached via the oxygen atom of an EO group or an AO group;
x is an integer whose number average is in the range of from 2 to 80;
y is an integer whose number average is in the range of from 0 to 50, the number
average of the sum of x and y being in the range of from 3 to 80;

Ra, Rb independently of one another are hydrogen or methyl; and
Rc is hydrogen, C1-C4-alkyl or phenyl
where at least one of the radicals Ra, Rb and Rc is different from hydrogen,
and where the polyether compound is selected from
ethylene oxide/propylene oxide copolymers,
polyether compounds in which the at least one polyether group of the formula III
is attached covalently via an oxygen, sulfur or nitrogen atom to a hydrocarbon
radical having 8 to 40 carbon atoms, and which optionally also has 1 or 2
carbonyloxy groups and/or 1, 2, 3 or 4 OH groups,
and mixtures thereof.
2. The active compound concentrate as claimed in claim 1 in which the nonionic
surfactant S has an HLB according to Griffin in the range of from 1.5 to 19.5.
3. The active compound concentrate as claimed in claim 1 in which the nonionic
surfactant S has a modified HLB in the range of from 5 to 19.5.
4. The active compound concentrate as claimed in claim 1 where the polyether
compound is selected from polyethoxylates and poly(ethoxylate-co-propoxylate)s of
C8-C22-alkanols, polyethoxylates and poly(ethoxylate-co-propoxylate)s of fatty acids,
polyethoxylates and poly(ethoxylate-co-propoxylate)s of fatty amines, polyethoxylates
and poly(ethoxylate-co-propoxylate)s of mono- and diglycerides of aliphatic C8-C22-
monocarboxylic acids, polyethoxylates and poly(ethoxylate-co-propoxylate)s of
sorbitan esters of aliphatic C8-C22-monocarboxylic acids, polyethoxylates and
poly(ethoxylate-co-propoxylate)s of alkylphenols, polyethoxylates and poly(ethoxylate-
co-propoxylate)s of di- and tristyrylphenols, polyethoxylates and poly(ethoxylate-co-
propoxylate)s of alkylpolyglycosides and mixtures thereof.
5. The active compound concentrate as claimed in any of claims 1 to 4 where the
polyether compound has a polyether radical of the formula III which is attached via
oxygen to a C8-C22-alkyl radical, where Rx in formula III is hydrogen, EO is CH2CH20,
AO is CH2CH(CH3)O, x is a number whose number average is in the range of from 3
to 49, y is a number whose number average is in the range of from 1 to 47 and the
number average of the sum x + y is in the range of from 5 to 50.
6. The active compound concentrate as claimed in claim 5 in which the polyether
compound is selected from compounds of the general formula IV
R11-O-[(EO)x(AO)y]-Rx,
in which R11 is alkyl having 8 to 30 carbon atoms and in which x, y, EO, AO and Rx
have the meanings given in claim 4.
7. The active compound concentrate as claimed in any of the preceding claims,
comprising components a) and b) in the form of their dissolved alkali metal or
ammonium salts.

ABSTRACT

AQUEOUS ACTIVE INGREDIENT CONCENTRATE HAVING AN HERBICIDAL EFFECT
The invention discloses an aqueous active compound concentrate comprising, in dissolved
form:
(a) 10 to 100 g/l of at least one 4-benzoyl-substituted pyrazole compound of the
formula I

or one of its agriculturally useful salts;
in which R1; R2; R3; R4; R5 and R6 are as defined in the specification.
(b) 50 to 250 g/l of at least one benzoic acid compound of the formula II

or one of its agriculturally useful salts;
in which R7and R8 are as defined in the specification.
(c) 100 to 500 g/l of at least one nonionic surfactant S, selected from polyether
compounds having repeat units derived from ethylene oxide,
alkylpolyglycosides and mixtures thereof, where the polyether compound has a
polyether group of formula III